As teachers and students increasingly dwell in a digital world, Wikipedia is a powerful presence. While it is wise to plan and teach cautiously with respect to Wikipedia, the author believes that teachers need to acknowledge its stronghold in students' lives and teach correspondingly. That is, social studies teachers must provide opportunities for their students to learn to critically read Wikipedia, while at the same time helping them understand how it is created, how it defines and positions knowledge, and what it makes possible and fails to do. Rather than battle Wikipedia's stronghold in students' lives, teachers should seize the opportunity to teach students how to read Wikipedia through a critical lens. In this article, the author takes up his initial experiences with Wikipedia, describing how he came to embrace it in his classroom. He considers how the attention devoted to Wikipedia in the pages of Social Education has presented a mixed message of trouble and usefulness. In examining both troubles and uses of Wikipedia, the author describes one central purpose he has in teaching with it: teaching about knowledge construction. He concludes by briefly expanding his focus to think about how teaching with a wiki can enhance his purpose for teaching with Wikipedia. (Contains 1 table and 27 notes.)